Process of making phenylamidoacetonitrile.



UNirnn nrnnr BENNO HOMOLKA, OF FRANKFORT-ON-THE-MAIN, AND NIOOLAUS SOHWAN, OF HOOI-ISTON-TI-IE-MA'IN, GERMANY, ASSIGNORS TO FARBWERKE, VORM. MEISTER, LUOIUS & BRUNING, OF HOOHST-ON-TI'IE-MAIN, GERMANY, A CORPORATION OF GERMANY.

PROCESS OF MAKING PHENYLAMIDOAOETONITRlLE.

SPEGIFIGATION' forming part of Letters Patent No. 701,044, dated May 27, 1902.

Application filed October 26,1901. Serial No. 80,038. (No specimens.)

To a whom, it nuty concern: from a mixture of ether and ligroin it has 40 Be it known that we, BENNO HOMOLKA, the known melting-point of 42 to 43 centi- Ih. D., residing at Frank'fort-on-the-Main, grade and yields when hydrolyzed in the and NICOLAUS SOHWAN, Ph. D., residing at known manner phenylglycocol.

5 l'Iochst-on-the-lilain,Germany,citizens of'the If in the above example the equivalent Empire of Germany, have invented certain quantity of orthotoluidin is used instead of 45 new and useful Improvements in the Manuanilin, ortho -tolylamidoacetonitrile is obfacture of Phenylamidoacetonitrile and IIotained in the same manner, which on hydrolniologues and Substitution Products Thereof, ysis yields ortho-tolyl-glycin. In the same [O of which the following is a specification. manner may be obtained with paratoluidin We have found that the nitrile of glycollic the known para tolylamidoacetonitrile or acid (OH)OH -CN reacts with anilin, its therefrom the para-tolylglycin. homologues, or substitution products with II. Manufacture of phcnylamidoacctoni: elimination of water and formation of phenyltrile-oriho-carbowyl'ic acid.-Sixteen parts, by I 5 amidoacetonitrile, its homologues, or substiweight, of sodium anthranilate are heated in tution products, the iypical equation for the aqueous or aqueous-alcoholic solution with reaction being: 5.7 parts of glycollic-acid nitrile til: the a11- thranilio acid has disa eared. fter the H NH OH ON reaction is complete (an d after distilling off 2 6 5 the alcohol, if used) the known phenylamido- This invention relates to the manufacture acetonitrile-ortho-carboxylic acid is precipiof phenylamidoacetonitrile and its homotated from the solution by a dilute acid. On logues and substitution products by the fore- I hydrolysis in the well-known manner it yields going reaction, which occurs slowly already phenylglycin-ortho-carboxylic acid. 25 at ordinary temperature, but rapidly and Having now described our invention,what

completely at a high temperature. we claim is- The following examples illustrate the The herein-described process of making process: phenylamidoacetonitrile, which consists in I. ilfcmtfiacture of 1971611ylamidoaceton'icausing glycollic-acid nitrile to act on anilin 3o (rile-9.3 parts, by weight, of anilin are dibases, substantially as set forth.

gested at water-bath temperature with 5.7 In testimony that we claim the foregoing as parts, by weight, of glycollic-acid nitrile in our invention we have signed our names in aqueous or aqueous-alcoholic solution till the presence of two subscribing witnesses. auilin has disappeared, or the solution may i 3 5 be allowed to stand at ordinary temperature. After all the anilin has disappeared and any alcohol employed has been distilled off the Witnesses: phenylamidoacetonitrile separates as an oil, ALFRED BRISBOIS, which soon solidifies. After recrystallization BERNHARD LYDECKER. 

